U.S. Pat. No. 4,892,944 (Mori et at) describes a process for producing quaternary ammonium salts and quaternary phosphonium salts by reacting a tertiary amine or phosphine with a carbonic acid diester to form the corresponding quaternary carbonate and thereafter mixing the carbonate with an acid resulting in decarboxylation. The quaternary salts are reported to be useful as catalysts for phase transfer reactions, electrolytes for aqueous and organic electrolytic solutions, various additives, medicaments, etc. The acids which may be utilized to form the quaternary salts may be inorganic acids such HF, HCl, HNO.sub.3, SO.sub.4, etc., or the acids may be organic acids such as 2-methyl-2-propyl pentanoic acid, acrylic acid, lactic acid; aliphatic polycarboxylic acids such as citric acid, malonic acid; aromatic carboxylic acids such as benzoic acid, toluic acid, etc.; aromatic polycarboxylic acids such as phthalic acid, etc.
Quaternary ammonium compounds are described in U.S. Pat. No. 3,972,855, and these compounds are described as being useful in the treatment of substrates such as plastic materials and textile materials to impart anti-static properties. In particular, the quaternary ammonium compounds described in the '855 patent contain a 2-hydroxy-oxy propylene group and an oxy alkylene group. The anion of the salt may be selected from the group consisting of chloride, bromide, iodide, nitrate, hydroxyl, phosphate, methyl sulfate, formate, acetate, propionate, citrate and tartrate.
U.S. Pat. No. 4,692,543 (Tenud et at) and U.S. Pat. No. 4,732,709 (Tenud et al) describe the preparation of optically-active di-(3-chloro-2-oxy-propyltrimethyl ammonium)-tartrate. The '709 patent is a divisional of the '543 patent. The two patents also describe a method for the production of optically-active carnitine nitric chloride from the optically-active tartrates. The process for the production of the optically-active tartrate comprises converting the racemic 3-chloro-2-oxypropyltrimethyl ammonium chloride by racemate resolution with L-(+)-tartaric acid in the presence of a trialkylamine into the di-[(-)-3-chloro-2-oxy-propyltrimethylammonium]-L-(+)-tartrate. Other processes for preparing the same optically-active tartrate are described in these patents.